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Synthetic method of 1-(5-chloro-6-methoxyl-2-naphthyl)acetone serving as naproxen medicinal intermediate

A synthesis method and intermediate technology, applied in the field of synthesis of naproxen drug intermediate 1-acetone, can solve the problems of good curative effect and achieve the effects of increasing reaction yield, reducing intermediate links, reducing reaction temperature and reaction time

Inactive Publication Date: 2017-02-15
XIAMEN AN PU DUN INFORMATION TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Can be safely used in combination with corticosteroids, but efficacy is no better when combined with corticosteroids than with corticosteroids alone

Method used

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  • Synthetic method of 1-(5-chloro-6-methoxyl-2-naphthyl)acetone serving as naproxen medicinal intermediate

Examples

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example 1

[0014] In a reaction vessel equipped with a stirrer, a thermometer, and a reflux condenser, add 1.17mol of anhydrous stannous chloride and 500ml of carbon disulfide, control the solution temperature at 45℃, stirring speed 130rpm, stirring time maintained at 40min, add propionamide dropwise (3) 1.17mol, the dropping time is controlled at 2h, and then 1-chloro-2-methoxy naphthalene (2) 1.2mol dissolved in 400mol carbon disulfide solution, the dropping time is controlled at 2h, and the solution temperature is maintained at 30 ℃, continue the reaction for 3h, pour the reactants into 1100g of 15% potassium bromide solution, separate the organic layer, extract the water layer with carbon disulfide for 6-8 times, combine the organic layers, and use 35% sodium sulfite sequentially Wash solution, wash with sodium nitrate solution, dry phosphorus pentoxide, distill under reduced pressure at 1.9kPa, recover the solvent, lower the temperature of the solution to 10°C, and precipitate solids....

example 2

[0016] In a reaction vessel equipped with a stirrer, a thermometer and a reflux condenser, add 1.18 mol of anhydrous stannous chloride and 550 ml of carbon disulfide, control the solution temperature at 47°C, stirring speed 135rpm, stirring time maintained at 45min, and add propionamide dropwise (3) 1.17mol, the dropping time is controlled at 2.5h, and then 1-chloro-2-methoxy naphthalene (2) 1.3mol dissolved in 400mol carbon disulfide solution, the dropping time is controlled at 2h, and the solution temperature is maintained at 32℃, continue to react for 3h, pour the reactants into 1100g of 17% potassium bromide solution with mass fraction, separate the organic layer, extract the water layer with carbon disulfide 7 times, combine the organic layers, and use 38% sodium sulfite solution in turn Wash, wash with potassium sulfate solution, dry phosphorus pentoxide, distill under reduced pressure at 2.1kPa, recover the solvent, lower the temperature of the solution to 12°C, and preci...

example 3

[0018] In a reaction vessel equipped with a stirrer, a thermometer and a reflux condenser, add 1.18 mol of anhydrous stannous chloride and 550 ml of carbon disulfide, control the temperature of the solution at 47°C, the stirring speed at 140 rpm, and the stirring time at 45 min. Add propionamide dropwise (3) 1.17mol, the dropping time is controlled at 2h, and then 1-chloro-2-methoxy naphthalene (2) 1.3mol dissolved in 400mol carbon disulfide solution, the dropping time is controlled at 3h, and the solution temperature is maintained at 35 ℃, continue to react for 4h, pour the reactants into 1100g of 20% potassium bromide solution, separate the organic layer, extract the aqueous layer with carbon disulfide 8 times, combine the organic layers, and wash with 40% sodium sulfite solution in turn , Wash with sodium nitrate solution, dry phosphorus pentoxide, distill under reduced pressure of 2.1kPa, recover the solvent, reduce the temperature of the solution to 15℃, and precipitate sol...

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Abstract

The invention discloses a synthetic method of 1-(5-chloro-6-methoxyl-2-naphthyl)acetone serving as a naproxen medicinal intermediate. The synthetic method comprises the following steps: adding 1.17 to 1.19mol of anhydrous stannous chloride and 500 to 600ml of carbon disulfide into a reaction vessel in which a stirrer, a thermometer and a reflux condenser are arranged; controlling the temperature of the solution at 45 to 50DEG C, and controlling the stirring speed at 130 to 150rpm; dropwise adding 1.17mol of propanamide, and controlling the dropping time at 2 to 3 hours; then dropwise adding 1.2 to 1.3mol of 1-chloro-2-methoxynaphthalene, dissolving into 400mol of carbon disulfide solution, keeping the temperature of the solution at 30 to 35DEG C, pouring a reactant into 1100g of potassium bromide solution, and separating to obtain organic layers; extracting a water layer with the carbon disulfide for 6 to 8 times, combining the organic layers, sequentially washing with a sodium sulfite solution and a saline solution, drying with phosphorus pentoxide, distilling under reduced pressure, reducing the temperature of the solution to be 10 to 15DEG C, and separating out a solid; adding the solid into 600ml of sodium chloride solution, maintaining the stirring speed at 170 to 190rpm, performing suction filtration, washing with a potassium nitrate solution until no oily matters exist, and dehydrating by using a dehydrating agent to obtain light yellow powder 1-(5-chloro-6-methoxyl-2-naphthyl)acetone.

Description

Technical field [0001] The invention relates to a method for synthesizing 1-(5-chloro-6-methoxy-2-naphthyl)acetone, a naproxen drug intermediate. Background technique [0002] Naproxen has anti-inflammatory, antipyretic and analgesic effects and is a PG synthase inhibitor. Oral absorption is rapid and complete. The plasma concentration reaches its peak 2 to 4 hours after one administration, and more than 99% of the blood is bound to plasma proteins, and the t1 / 2 is 13 to 14 hours. About 95% are excreted in the urine as original form and metabolites. For rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, gout, chronic degenerative diseases of the motor system (such as joints, muscles and tendons), and mild to moderate pain such as dysmenorrhea, it has a positive effect. Moderate pain can be relieved 1 hour after taking the medicine, and the analgesic effect can last for more than 7 hours. The curative effect for rheumatoid arthritis and osteoarthritis is similar to a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/45C07C49/84
CPCC07C45/455
Inventor 储冬红
Owner XIAMEN AN PU DUN INFORMATION TECH CO LTD